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Factors Controlling the Equilibrium of Pt‐Catalyzed [1,2]‐ versus [1,3]‐Acyloxy Migration
Author(s) -
Cho Eun Jin
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201103799
Subject(s) - catalysis , substituent , allene , chemistry , carbenoid , alkyne , electrophile , medicinal chemistry , transition metal , stereochemistry , photochemistry , rhodium , organic chemistry
Pick a pathway : Upon activation with an electrophilic transition‐metal catalyst, a propargylic acetate undergoes competing [1,2]‐ and [1,3]‐acyloxy migration depending on the reaction temperature as well as the substituent pattern around the alkyne. The nature of the catalyst also affects the reaction course. The reactions provided clear evidence for the interconversion between carbenoid and allene intermediates (see scheme).